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  • Writer's pictureRachel Ober

Rachel's Perfect Day in Old San Juan

Updated: Mar 11, 2022

I absolutely LOVE Old San Juan (locally known as "VSJ" for Viejo San Juan - Spanish for Old San Juan). It is so vibrant and alive with energy, great food, and travel photo spots! I compare VSJ to a blend of Charleston and Miami. My perfect day in VSJ looks something like this:


Brunch: On your way to Old San Juan, eat at SOCIAL in Condado. Technically in Condado, not Old San Juan, but it will likely be along the route as you head to VSJ. SOCIAL has amazing views, especially if you can get a table on the water. The donut chicken sandwich is unique and possibly life-changing...but good thing you are going to be walking a lot today, right? Typically, you would grab an Uber to VSJ from Condado, but you can also walk if you aren't in a hurry. It takes about 40 minutes to walk from Candado to VSJ, but most of the walk is along the ocean and very enjoyable.



Castillo de San Cristobal: An old Spanish fort that is an icon of San Juan. My preferred spot for photos or what you may consider the 'Instagrammable spot' is actually a side entrance off Calle Norzagaray (see map). Great photos if you pass through the courtyard.


Walking tour of Old San Juan: Honestly, the best way to explore VSJ is to just give yourself time and wander. Pro-tip for first-timers...wear comfortable shoes. Every street is worth walking. There is so much local culture and great photos abound. Calle de la Luna and Calle de Tetuan are particularly aesthetic and not a lot of traffic so you can get the perfect rainbow + cobblestone street shot.


Other Instagrammable places in Old San Juan: The Puerto Rico Alley Flag (side alley at the corner of Calle del Cristo and C. de la Fortaleza. Callejon de la Puerta Bandera Painted Puerto Rican Flag Door (Calle Imperial). Another low traffic street with great views -- Caleta de las Monjas.

Drinks at sunset: The Mezzanine is a throw-back, cute, eclectic cocktail bar. Get anything on the drink menu with passion fruit (probably a good tip for Puerto Rico in general). If you can't get a good balcony seat that overlooks the cobblestone streets at The Mezzanine, head up one floor to the Al Fresco Rooftop Wine Bar. We slightly prefer Mezzanine, but both are great spots.


Dinner: Barrachina is an iconic VSJ restaurant and will pop up on many "to do" travel guides, with good reason. Barrachina is, allegedly, where the Pina Colada drink was originally invented. Their mofongo (local mashed plantain dish) is outstanding. Entering into Barrachina feels like you are entering a Caribbean speak-easy.


Dessert: Right next to Barrachina, hit up the uber-popular Anita La Mamma del Gelato to satisfy that sweet tooth (we walked a lot today, remember?)


Nightcap: Cannon Club - Steinway Piano Bar (The Gallery Inn). This place is an absolute gem. A little garden oasis with stellar drinks in the heart of the city. The owner, Jan D'Esopo, is a famous painter, local legend, and the best looking 85 year old you will ever meet. You'll almost always see Jan with her signature parrot at the Cannon Club.


What a day! Now off to bed and time to hit the beaches tomorrow. I've included other places to eat below, as well as places to stay and things to do! Don't forget to follow me on Instagram - here :)


P.S: Parking and trafficking in VSJ can be challenging. Even if you have a car, I recommend taking an Uber. The San Juan metro does not go to VSJ. If you go to VSJ during a time of high traffic (winter tourist season and after 4pm in particular), ask the driver to drop you at the Starbucks at the corner of Calle de la Fortaleza and Calle de Tetuan.


P.P.S.: I mentioned this earlier but wear walking shoes. Stilettoes and cobblestone are a surprisingly poor life choice...


The Gallery Inn (which is apart of the Piano Bar mentioned above), Hotel El Convento, CasaBlanca Hotel, Navona Studios Guesthouse (one of the most affordable - below $100), Decanter Hotel, Monastery Art Suites

Barrachina, Princesa, Antojitos del Callejon and La Vergüenza Puertorrican Chinchorro (both very lively at night - DJ on Friday + Dancing on Sundays), Vaca Brava (If you have a group of people order the meat clothesline -- you get SO much food), La Lanterna (heads up -- this is an Italian restaurant but a special place if you are traveling with your spouse!)


Castillo de San Cristobal, grab a popsicle at Senor Paleta (my favorite is Mango!), Salsa Dancing at Shing-A-Ling (Inside La Factoría and one of the top 50 bars in the world), Overlook La Perla where the music video Despacito was filmed + you can also see the Carmelo Anthony basketball court (the neighborhood is not recommended for visitors to enter for safety reasons), The historic lighthouse tower at El Morro, and there are plenty of tours you can sign up for if you want to learn more about the history of Old San Juan!

Dress is from Modern Soul and this is Calle de La Luna!

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